Chemistry: An Introduction to General, Organic, and Biological Chemistry 13e PDF Textbook

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GLOBAL GLOBAL EDITION EDITION For these Global Editions, the editorial team at Pearson has An Introduction to General, Organic, and Biological Chemistry collaborated with educators across the world to address a wide range of subjects and requirements, equipping students with the best possible learning tools. This Global Edition preserves the cutting-edge approach and pedagogy of the original, but also features alterations, customization, and adaptation from the North American version. Chemistry Chemistry An Introduction to General, Organic, THIRTEENTH and Biological Chemistry EDITION THIRTEENTH EDITION Timberlake Timberlake This is a special edition of an established title widely used by colleges and universities throughout the world. Pearson published this exclusive edition for the benefit of students outside the United States and Canada. If you EDITION GLOBAL purchased this book within the United States or Canada, you should be aware that it has been imported without the approval of the Publisher or Author. Pearson Global Edition Timberlake_13_1292228865_Final.indd 1 08/02/18 7:47 PM Chemistry An Introduction to General, Organic, and Biological Chemistry Chemistry An Introduction to General, Organic, and Biological Chemistry Thirteenth Edition Global Edition Karen Timberlake Contributions by MaryKay Orgill, Ph.D. Professor of Chemistry, University of Nevada, Las Vegas 330 Hudson Street, NY NY 10013  Courseware Portfolio Manager: Scott Dustan Full Service Vendor: SPi Global Director, Courseware Portfolio Management: Jeanne Zalesky Full Service Project Manager: Karen Berry/Christian Arsenault Assistant Acquisitions Editor, Global Edition: Aditee Agarwal Copyeditor: Laura Patchkofsky Assistant Project Editors, Global Edition: Aurko Mitra, Aman Kumar Design Manager: Mark Ong Manager, Media Production, Global Edition: Vikram Kumar Cover Designer: Lumina Datamatics, Inc. Senior Manufacturing Controller, Global Edition: Kay Holman Interior Designer: Tamara Newnam Content Producer: Lizette Faraji Photo and Illustration Support: Stephanie Marquez, Imagineering Art Managing Producer: Kristen Flathman Rights and Permissions Project Manager: Kathleen Zander Courseware Analyst: Coleen Morrison Rights and Permissions Management: Ben Ferrini Courseware Director, Content Development: Jennifer Hart Manufacturing Buyer: Maura Zaldivar-Garcia Courseware Editorial Assistant: Fran Falk Marketing Manager: Elizabeth Ellsworth Bell Rich Media Content Producer: Jenny Moryan Cover Image Credit: © nikkytok/Shutterstock Credits and acknowledgments borrowed from other sources and reproduced, with permission, in this textbook appear on p. 695. Pearson Education Limited KAO Two KAO Park Harlow CM17 9NA United Kingdom and Associated Companies throughout the world Visit us on the World Wide Web at: www.pearsonglobaleditions.com © Pearson Education Limited 2019 The rights of Karen Timberlake to be identified as the author of this work have been asserted by her in accordance with the Copyright, Designs and Patents Act 1988. Authorized adaptation from the United States edition, entitled Chemistry: An Introduction to General, Organic, and Biological Chemistry, 13th Edition, ISBN 978-0-134-42135-3 by Karen Timberlake, published by Pearson Education © 2018. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without either the prior written permission of the publisher or a license permitting restricted copying in the United Kingdom issued by the Copyright Licensing Agency Ltd, Saffron House, 6–10 Kirby Street, London EC1N 8TS. All trademarks used herein are the property of their respective owners. The use of any trademark in this text does not vest in the author or publisher any trademark ownership rights in such trademarks, nor does the use of such trademarks imply any affiliation with or endorsement of this book by such owners. ISBN 10: 1-292-22886-5 ISBN 13: 978-1-292-22886-0 British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library 10 9 8 7 6 5 4 3 2 1 Print edition typeset in 10/12pt Times LT Pro by SPi Global Printed and bound by Vivar in Malaysia A01_TIMB8860_13_GE_FM.indd 4 16/03/2018 10:47 Brief Contents 1 Chemistry in Our Lives 31 2 Chemistry and Measurements 55 3 Matter and Energy 90 4 Atoms and Elements 128 5 Nuclear Chemistry 166 6 Ionic and Molecular Compounds 198 7 Chemical Quantities and Reactions 246 8 Gases 289 9 Solutions 315 10 Acids and Bases and Equilibrium 354 11 Introduction to Organic Chemistry: Hydrocarbons 393 12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones 428 13 Carbohydrates 462 14 Carboxylic Acids, Esters, Amines, and Amides 500 15 Lipids 539 16 Amino Acids, Proteins, and Enzymes 578 17 Nucleic Acids and Protein Synthesis 614 18 Metabolic Pathways and ATP Production 649 5 Table of Contents 1 Clinical Update Greg’s Visit with His Doctor 82 Concept Map 82 Chemistry in Chapter Review 82 Our Lives 31 Key Terms 83 Key Math Skill 84 CAREER Forensic Scientist 31 Core Chemistry Skills 84 CLINICAL UPDATE Forensic Evidence Helps Solve the Understanding the Concepts 85 Crime 31 Additional Practice Problems 86 1.1 Chemistry and Chemicals 32 Challenge Problems 87 1.2 Scientific Method: Thinking Like a Scientist 33 Answers 88 CHEMISTRY LINK TO HEALTH Early Chemist: Paracelsus 34 3 1.3 Studying and Learning Chemistry 35 1.4 Key Math Skills for Chemistry 39 1.5 Writing Numbers in Scientific Notation 46 Clinical Update Matter and Energy 90 Forensic Evidence Helps Solve the Crime 49 Concept Map 50 Career Dietitian 90 Chapter Review 50 CLINICAL UPDATE A Diet and Exercise Program 90 Key Terms 51 3.1 Classification of Matter 91 Key Math Skills 51 CHEMISTRY LINK TO HEALTH Understanding the Concepts 52 Breathing Mixtures 93 Additional Practice Problems 53 3.2 States and Properties of Matter 94 Challenge Problems 53 3.3 Temperature 97 Answers 54 CHEMISTRY LINK TO HEALTH Variation in Body Temperature 101 2 3.4 Energy 101 CHEMISTRY LINK TO THE ENVIRONMENT Carbon Dioxide and Climate Change 103 Chemistry and 3.5 Energy and Nutrition 104 Measurements 55 CHEMISTRY LINK TO HEALTH Losing and Gaining Weight 106 CAREER Registered Nurse 55 3.6 Specific Heat 107 CLINICAL UPDATE Greg’s Visit with His Doctor 55 3.7 Changes of State 110 2.1 Units of Measurement 56 CHEMISTRY LINK TO HEALTH 2.2 Measured Numbers and Significant Steam Burns 116 Figures 59 Clinical Update 2.3 Significant Figures in Calculations 61 A Diet and Exercise Program 117 2.4 Prefixes and Equalities 65 Concept Map 118 2.5 Writing Conversion Factors 69 Chapter Review 118 2.6 Problem Solving Using Unit Conversion 72 Key Terms 119 2.7 Density 76 Core Chemistry Skills 120 CHEMISTRY LINK TO HEALTH Understanding the Concepts 121 Bone Density 79 Additional Practice Problems 122 6  Contents 7 Challenge Problems 124 CHEMISTRY LINK TO HEALTH Answers 124 Radon in Our Homes 172 COMBINING IDEAS from Chapters 1 to 3 126 5.3 Radiation Measurement 177 CHEMISTRY LINK TO HEALTH Radiation and Food 178 4 5.4 Half-Life of a Radioisotope 180 CHEMISTRY LINK TO THE ENVIRONMENT Dating Ancient Objects 182 Atoms and 5.5 Medical Applications Using Radioactivity 184 Elements 128 CHEMISTRY LINK TO HEALTH Brachytherapy 187 CAREER Farmer 128 5.6 Nuclear Fission and Fusion 188 CLINICAL UPDATE Improving Crop Production 128 CHEMISTRY LINK TO THE ENVIRONMENT 4.1 Elements and Symbols 129 Nuclear Power Plants 191 CHEMISTRY LINK TO HEALTH Clinical Update Toxicity of Mercury 130 Cardiac Imaging Using a Radioisotope 191 4.2 The Periodic Table 131 Concept Map 192 CHEMISTRY LINK TO HEALTH Chapter Review 192 Elements Essential to Health 134 Key Terms 193 4.3 The Atom 136 Core Chemistry Skills 193 4.4 Atomic Number and Mass Number 139 Understanding the Concepts 194 CHEMISTRY LINK TO THE ENVIRONMENT Additional Practice Problems 195 Many Forms of Carbon 141 Challenge Problems 195 4.5 Isotopes and Atomic Mass 142 Answers 196 4.6 Electron Energy Levels 145 CHEMISTRY LINK TO HEALTH Biological Reactions to UV Light 149 4.7 Trends in Periodic Properties 150 Clinical Update 6 Improving Crop Production 157 Ionic and Molecular Concept Map 158 Compounds 198 Chapter Review 158 Key Terms 159 CAREER Pharmacy Technician 198 Core Chemistry Skills 160 CLINICAL UPDATE Compounds at the Pharmacy 198 Understanding the Concepts 161 6.1 Ions: Transfer of Electrons 199 Additional Practice Problems 162 CHEMISTRY LINK TO HEALTH Challenge Problems 163 Some Important Ions in the Body 202 Answers 163 6.2 Ionic Compounds 204 6.3 Naming and Writing Ionic Formulas 206 5 6.4 Polyatomic Ions 211 6.5 Molecular Compounds: Sharing Electrons 215 6.6 Lewis Structures for Molecules 219 Nuclear 6.7 Electronegativity and Bond Polarity 223 6.8 Shapes of Molecules 226 Chemistry 166 6.9 Polarity of Molecules and Intermolecular Forces 229 Clinical Update CAREER Radiation Technologist 166 Compounds at the Pharmacy 233 CLINICAL UPDATE Cardiac Imaging Using a Radioisotope 166 Concept Map 234 5.1 Natural Radioactivity 167 Chapter Review 234 5.2 Nuclear Reactions 170 Key Terms 235 Core Chemistry Skills 236 8 Contents Understanding the Concepts 238 CHEMISTRY LINK TO HEALTH Additional Practice Problems 239 Measuring Blood Pressure 292 Challenge Problems 240 8.2 Pressure and Volume (Boyle’s Law) 295 Answers 241 CHEMISTRY LINK TO HEALTH Pressure–Volume Relationship in Breathing 296 COMBINING IDEAS from Chapters 4 to 6 244 8.3 Temperature and Volume (Charles’s Law) 298 8.4 Temperature and Pressure (Gay-Lussac’s Law) 300 8.5 The Combined Gas Law 302 7 8.6 Volume and Moles (Avogadro’s Law) 303 8.7 Partial Pressures (Dalton’s Law) 306 CHEMISTRY LINK TO HEALTH Chemical Quantities Hyperbaric Chambers 308 and Reactions 246 Clinical Update Exercise-Induced Asthma 309 CAREER Exercise Physiologist 246 Concept Map 309 CLINICAL UPDATE Improving Natalie’s Overall Chapter Review 310 Fitness 246 Key Terms 310 7.1 The Mole 247 Core Chemistry Skills 311 7.2 Molar Mass 251 Understanding the Concepts 311 7.3 Calculations Using Molar Mass 253 Additional Practice Problems 312 7.4 Equations for Chemical Reactions 256 Challenge Problems 313 7.5 Types of Chemical Reactions 263 Answers 313 CHEMISTRY LINK TO HEALTH Incomplete Combustion: Toxicity of Carbon Monoxide 267 7.6 Oxidation–Reduction Reactions 268 9 7.7 Mole Relationships in Chemical Equations 271 7.8 Mass Calculations for Chemical Reactions 274 7.9 Energy in Chemical Reactions 276 CHEMISTRY LINK TO HEALTH Solutions 315 Cold Packs and Hot Packs 277 Clinical Update CAREER Dialysis Nurse 315 Improving Natalie’s Overall Fitness 279 CLINICAL UPDATE Using Dialysis for Renal Failure 315 Concept Map 280 9.1 Solutions 316 Chapter Review 280 CHEMISTRY LINK TO HEALTH Key Terms 281 Water in the Body 318 Core Chemistry Skills 282 9.2 Electrolytes and Nonelectrolytes 320 Understanding the Concepts 283 CHEMISTRY LINK TO HEALTH Additional Practice Problems 285 Electrolytes in Body Fluids 322 Challenge Problems 286 9.3 Solubility 324 Answers 287 CHEMISTRY LINK TO HEALTH Gout and Kidney Stones: A Problem of Saturation in Body Fluids 325 8 9.4 Solution Concentrations 328 9.5 Dilution of Solutions 336 9.6 Properties of Solutions 339 Gases 289 CHEMISTRY LINK TO HEALTH Dialysis by the Kidneys and the Artificial CAREER Respiratory Therapist 289 Kidney 342 CLINICAL UPDATE Exercise-Induced Asthma 289 Clinical Update 8.1 Properties of Gases 290 Using Dialysis for Renal Failure 344  Contents 9 11 Concept Map 344 Chapter Review 344 Key Terms 345 Core Chemistry Skills 346 Introduction to Understanding the Concepts 346 Organic Chemistry: Additional Practice Problems 347 Challenge Problems 348 Hydrocarbons 393 Answers 349 CAREER Firefighter/Emergency Medical Technician 393 COMBINING IDEAS from Chapters 7 to 9 351 CLINICAL UPDATE Diane’s Treatment in the Burn Unit 393 11.1 Organic Compounds 394 11.2 Alkanes 396 11.3 Alkanes with Substituents 400 10 11.4 Properties of Alkanes 405 11.5 Alkenes and Alkynes 406 11.6 Cis–Trans Isomers 409 Acids and Bases CHEMISTRY LINK TO THE ENVIRONMENT Pheromones in Insect Communication 411 and Equilibrium 354 CHEMISTRY LINK TO HEALTH Cis–Trans Isomers for Night Vision 412 CAREER Clinical Laboratory Technician 354 11.7 Addition Reactions for Alkenes 412 CLINICAL UPDATE Acid Reflux Disease 354 CHEMISTRY LINK TO HEALTH 10.1 Acids and Bases 355 Hydrogenation of Unsaturated Fats 413 10.2 Brønsted–Lowry Acids and Bases 357 11.8 Aromatic Compounds 415 10.3 Strengths of Acids and Bases 360 CHEMISTRY LINK TO HEALTH 10.4 Acid–Base Equilibrium 363 Some Common Aromatic Compounds 417 CHEMISTRY LINK TO HEALTH CHEMISTRY LINK TO HEALTH Oxygen–Hemoglobin Equilibrium and Polycyclic Aromatic Hydrocarbons (PAHs) 418 Hypoxia 366 Clinical Update 10.5 Dissociation of Water 368 Diane’s Treatment in the Burn Unit 419 10.6 The pH Scale 370 CHEMISTRY LINK TO HEALTH Concept Map 419 Chapter Review 420 Stomach Acid, HCl 375 Summary of Naming 421 10.7 Reactions of Acids and Bases 376 Summary of Reactions 421 CHEMISTRY LINK TO HEALTH Key Terms 421 Antacids 379 Core Chemistry Skills 422 10.8 Buffers 380 Understanding the Concepts 422 CHEMISTRY LINK TO HEALTH Additional Practice Problems 423 Buffers in the Blood Plasma 382 Challenge Problems 424 Clinical Update Answers 425 Acid Reflux Disease 384 Concept Map 385 Chapter Review 385 Key Terms 387 12 Key Math Skills 387 Alcohols, Thiols, Core Chemistry Skills 387 Ethers, Aldehydes, Understanding the Concepts 388 and Ketones 428 Additional Practice Problems 389 Challenge Problems 390 CAREER Dermatology Nurse 428 Answers 391 CLINICAL UPDATE Diana’s Skin Protection Plan 428 12.1 Alcohols, Phenols, Thiols, and Ethers 429 10 Contents CHEMISTRY LINK TO HEALTH CHEMISTRY LINK TO HEALTH Some Important Alcohols and Phenols 432 Testing for Glucose 482 CHEMISTRY LINK TO HEALTH 13.6 Disaccharides 483 Ethers as Anesthetics 434 CHEMISTRY LINK TO HEALTH 12.2 Properties of Alcohols 435 How Sweet Is My Sweetener? 485 CHEMISTRY LINK TO HEALTH CHEMISTRY LINK TO HEALTH Hand Sanitizers 437 Blood Types and Carbohydrates 486 12.3 Aldehydes and Ketones 438 13.7 Polysaccharides 489 CHEMISTRY LINK TO HEALTH Clinical Update Some Important Aldehydes and Ketones 442 Kate’s Program for Type 2 Diabetes 491 12.4 Reactions of Alcohols, Thiols, Aldehydes, Concept Map 492 and Ketones 444 Chapter Review 492 CHEMISTRY LINK TO HEALTH Summary of Carbohydrates 493 Oxidation of Alcohol in the Body 447 Summary of Reactions 494 Clinical Update Key Terms 494 Diana’s Skin Protection Plan 451 Core Chemistry Skills 495 Concept Map 451 Understanding the Concepts 495 Chapter Review 452 Additional Practice Problems 496 Summary of Naming 453 Challenge Problems 497 Summary of Reactions 453 Answers 498 Key Terms 453 Core Chemistry Skills 454 14 Understanding the Concepts 454 Additional Practice Problems 455 Challenge Problems 457 Answers 457 Carboxylic Acids, COMBINING IDEAS from Chapters 10 to 12 460 Esters, Amines, and Amides 500 CAREER Environmental Health Practitioner 500 CLINICAL UPDATE Testing Soil and Water Samples for 13 Chemicals 500 14.1 Carboxylic Acids 501 14.2 Properties of Carboxylic Acids 503 Carbohydrates 462 CHEMISTRY LINK TO HEALTH Carboxylic Acids in Metabolism 506 CAREER Diabetes Nurse 462 14.3 Esters 507 CLINICAL UPDATE Kate’s Program for Type 2 CHEMISTRY LINK TO HEALTH Diabetes 462 Salicylic Acid from a Willow Tree 509 13.1 Carbohydrates 463 CHEMISTRY LINK TO THE ENVIRONMENT 13.2 Chiral Molecules 466 Plastics 510 CHEMISTRY LINK TO HEALTH 14.4 Hydrolysis of Esters 512 Enantiomers in Biological Systems 471 14.5 Amines 514 13.3 Fischer Projections of Monosaccharides 473 CHEMISTRY LINK TO HEALTH CHEMISTRY LINK TO HEALTH Amines in Health and Medicine 516 Hyperglycemia and Hypoglycemia 475 CHEMISTRY LINK TO THE ENVIRONMENT 13.4 Haworth Structures of Monosaccharides 476 Alkaloids: Amines in Plants 520 13.5 Chemical Properties of Monosaccharides 480 14.6 Amides 521  Contents 11 CHEMISTRY LINK TO HEALTH Additional Practice Problems 572 Amides in Health and Medicine 524 Challenge Problems 572 Clinical Update Answers 573 Testing Soil and Water Samples for Chemicals 527 COMBINING IDEAS from Chapters 13 to 15 576 Concept Map 528 Chapter Review 528 Summary of Naming 529 Summary of Reactions 529 Key Terms 531 16 Core Chemistry Skills 531 Understanding the Concepts 531 Amino Acids, Additional Practice Problems 532 Proteins, Challenge Problems 534 and Enzymes 578 Answers 535 CAREER Physician Assistant 578 CLINICAL UPDATE Jeremy’s Diagnosis and Treatment 15 for Sickle-Cell Anemia 578 16.1 Proteins and Amino Acids 579 16.2 Proteins: Primary Structure 583 Lipids 539 CHEMISTRY LINK TO HEALTH Essential Amino Acids and Complete CAREER Clinical Lipid Specialist 539 Proteins 585 CLINICAL UPDATE Rebecca’s Program to Lower CHEMISTRY LINK TO HEALTH Cholesterol 539 Polypeptides in the Body 587 15.1 Lipids 540 16.3 Proteins: Secondary, Tertiary, and Quaternary 15.2 Fatty Acids 541 Structures 588 CHEMISTRY LINK TO HEALTH CHEMISTRY LINK TO HEALTH Omega-3 Fatty Acids in Fish Oils 545 Protein Secondary Structures and 15.3 Waxes and Triacylglycerols 547 Alzheimer’s Disease 590 15.4 Chemical Properties of Triacylglycerols 551 CHEMISTRY LINK TO HEALTH CHEMISTRY LINK TO HEALTH Sickle-Cell Anemia 595 Converting Unsaturated Fats to Saturated 16.4 Enzymes 596 Fats: Hydrogenation 552 CHEMISTRY LINK TO HEALTH 15.5 Phospholipids 555 Isoenzymes as Diagnostic Tools 599 CHEMISTRY LINK TO HEALTH 16.5 Factors Affecting Enzyme Activity 601 Infant Respiratory Distress Syndrome (IRDS) 559 Clinical Update 15.6 Steroids: Cholesterol, Bile Salts, and Jeremy’s Diagnosis and Treatment for Steroid Hormones 560 Sickle-Cell Anemia 606 CHEMISTRY LINK TO HEALTH Anabolic Steroids 564 Concept Map 607 15.7 Cell Membranes 566 Chapter Review 607 Clinical Update Key Terms 608 Rebecca’s Program to Lower Cholesterol 568 Core Chemistry Skills 609 Understanding the Concepts 609 Concept Map 569 Additional Practice Problems 610 Chapter Review 569 Challenge Problems 611 Summary of Reactions 570 Understanding Protein Structures 611 Key Terms 570 Answers 611 Core Chemistry Skills 571 Understanding the Concepts 571 12 Contents 17 CHEMISTRY LINK TO HEALTH Lactose Intolerance 654 18.3 Coenzymes in Metabolic Pathways 656 Nucleic Acids 18.4 Glycolysis: Oxidation of Glucose 660 and Protein 18.5 The Citric Acid Cycle 665 18.6 Electron Transport and Oxidative Synthesis 614 Phosphorylation 669 CHEMISTRY LINK TO HEALTH CAREER Histology Technician 614 ATP Synthase and Heating the Body 672 CLINICAL UPDATE Ellen’s Medical Treatment 18.7 Oxidation of Fatty Acids 675 Following Breast Cancer CHEMISTRY LINK TO HEALTH Surgery 614 Stored Fat and Obesity 678 17.1 Components of Nucleic Acids 615 CHEMISTRY LINK TO HEALTH 17.2 Primary Structure of Nucleic Acids 618 Ketone Bodies and Diabetes 681 17.3 DNA Double Helix and Replication 620 18.8 Degradation of Amino Acids 681 17.4 RNA and Transcription 623 Clinical Update 17.5 The Genetic Code and Protein Synthesis 626 Treatment of Luke’s Hepatitis C 684 CHEMISTRY LINK TO HEALTH Many Antibiotics Inhibit Protein Synthesis 629 Concept Map 685 17.6 Genetic Mutations 630 Chapter Review 686 17.7 Recombinant DNA 635 Summary of Reactions 687 17.8 Viruses 637 Key Terms 689 CHEMISTRY LINK TO HEALTH Core Chemistry Skills 689 Cancer 640 Understanding the Concepts 690 Clinical Update Additional Practice Problems 691 Ellen’s Medical Treatment Following Breast Challenge Problems 691 Cancer Surgery 641 Answers 691 Concept Map 642 COMBINING IDEAS from Chapters 16 to 18 693 Chapter Review 642 Key Terms 643 Credits  695 Core Chemistry Skills 644 Glossary/Index  699 Understanding the Concepts 644 Additional Practice Problems 645 Challenge Problems 646 Answers 646 18 Metabolic Pathways and ATP Production 649 CAREER Public Health Nurse (PHN) 649 CLINICAL UPDATE Treatment of Luke’s Hepatitis C 649 18.1 Metabolism and ATP Energy 650 18.2 Digestion of Foods 653 Applications and Activities KEY MATH SKILLS Identifying Oxidized and Reduced Substances 269 Using Mole–Mole Factors 272 Identifying Place Values 40 Converting Grams to Grams 274 Using Positive and Negative Numbers in Calculations 41 Using the Gas Laws 296 Calculating Percentages 42 Calculating Partial Pressure 306 Solving Equations 43 Using Solubility Rules 327 Interpreting Graphs 44 Calculating Concentration 329 Writing Numbers in Scientific Notation 47 Using Concentration as a Conversion Factor 330 Rounding Off 62 Identifying Conjugate Acid–Base Pairs 358 Calculating pH from [H3O+] 372 Using Le Châtelier’s Principle 365 Calculating [H3O+] from pH 374 Calculating [H3O+] and [OH -] in Solutions 369 Writing Equations for Reactions of Acids and Bases 376 CORE CHEMISTRY SKILLS Calculating Molarity or Volume of an Acid or Base in a Counting Significant Figures 59 Titration 378 Using Significant Figures in Calculations 62 Naming and Drawing Alkanes 397 Using Prefixes 66 Writing Equations for Hydrogenation and Hydration 412 Writing Conversion Factors from Equalities 69 Identifying Functional Groups 429 Using Conversion Factors 73 Naming Alcohols and Phenols 429 Using Density as a Conversion Factor 79 Naming Aldehydes and Ketones 439 Identifying Physical and Chemical Changes 96 Writing Equations for the Dehydration of Alcohols 444 Converting between Temperature Scales 97 Writing Equations for the Oxidation of Alcohols 445 Using Energy Units 102 Identifying Chiral Molecules 467 Using the Heat Equation 108 Identifying d and l Fischer Projections for Calculating Heat for Change of State 111 Carbohydrates 473 Counting Protons and Neutrons 139 Drawing Haworth Structures 476 Writing Atomic Symbols for Isotopes 142 Naming Carboxylic Acids 501 Writing Electron Arrangements 147 Hydrolyzing Esters 512 Identifying Trends in Periodic Properties 150 Forming Amides 522 Drawing Lewis Symbols 152 Identifying Fatty Acids 541 Writing Nuclear Equations 170 Drawing Structures for Triacylglycerols 548 Using Half-Lives 181 Drawing the Products for the Hydrogenation, Hydrolysis, Writing Positive and Negative Ions 200 and Saponification of a Triacylglycerol 552 Writing Ionic Formulas 205 Identifying the Steroid Nucleus 560 Naming Ionic Compounds 206 Drawing the Structure for an Amino Acid at Writing the Names and Formulas for Molecular Physiological pH 582 Compounds 216 Identifying the Primary, Secondary, Tertiary, and Drawing Lewis Structures 220 Quaternary Structures of Proteins 588 Using Electronegativity 223 Describing Enzyme Action 599 Predicting Shape 226 Writing the Complementary DNA Strand 622 Identifying Polarity of Molecules and Intermolecular Writing the mRNA Segment for a DNA Template 626 Forces 229 Writing the Amino Acid for an mRNA Codon 627 Converting Particles to Moles 247 Identifying the Compounds in Glycolysis 660 Calculating Molar Mass 252 Describing the Reactions in the Citric Acid Cycle 667 Using Molar Mass as a Conversion Factor 253 Calculating the ATP Produced from Glucose 672 Balancing a Chemical Equation 259 Calculating the ATP from Fatty Acid Oxidation Classifying Types of Chemical Reactions 263 (b Oxidation) 678 13 14 Applications and Activities Interactive Videos Solving Equations 44 Conversion Factors 73 Chemical vs. Physical Changes 96 Rutherford’s Gold-Foil Experiment 137 Writing Equations for an Isotope Produced by Bombardment 175 Half-Lives 181 Problem 7.65 275 Kinetic Molecular Theory 290 Solutions 335 Titration of an Acid 379 Naming Alkanes 402 Addition to an Asymmetric Bond 414 Oxidation of Alcohols 446 Chirality 466 Study Check 14.7 514 Membrane Structure 566 Different Levels of Protein Structure 593 Protein Synthesis 628 About the Author Chemistry: An Introduction to General, Organic, and Biological Chemistry, eighth edition, which has demon- strated her excellence over time. She received the “Texty” Textbook Excellence Award from the Text­book Authors Association for the first edition of Basic Chemistry. She has participated in education grants for science teaching including the Los Angeles Collaborative for Teaching Excellence (LACTE) and a Title III grant at her college. She speaks at conferences and educational meetings on the use of student-centered teaching methods in chemistry to promote the learning success of students. When Professor Timberlake is not writing textbooks, she and her husband relax by playing tennis, ballroom dancing, traveling, trying new restaurants, cooking, and taking care of their grandchildren, Daniel and Emily. KAREN TIMBERLAKE is Professor Emerita of chemistry at Los Angeles Valley College, where she taught chemistry for allied health and preparatory chemistry for DEDICATION 36 years. She received her bachelor’s degree in chemistry I dedicate this book to from the University of Washington and her master’s degree in biochemistry from the University of California My husband, Bill, for his patience, loving at Los Angeles. support, and preparation of late meals Professor Timberlake has been writing chemistry text- My son, John, daughter-in-law, Cindy, books for 40 years. During that time, her name has become grandson, Daniel, and granddaughter, Emily, associated with the strategic use of pedagogical tools that for the precious things in life promote student success in chemistry and the application of chemistry to real-life situations. More than one million The wonderful students over many years whose students have learned chemistry using texts, laboratory hard work and commitment always motivated manuals, and study guides written by Karen Timberlake. me and put purpose in my writing In addition to An Introduction to General, Organic and Biological Chemistry, thirteenth edition, she is also the au- thor of General, Organic, and Biological Chemistry, fifth FAVORITE QUOTES edition, with the a­ ccompanying Study Guide and Selected Solutions Manual, Laboratory Manual and ­ Essentials The whole art of teaching is only the art of awakening the Laboratory Manual, and Basic Chemistry, fifth edition, natural curiosity of young minds. with the ­accompanying Study Guide and Selected Solu- —Anatole France tions Manual. One must learn by doing the thing; though you think you Professor Timberlake belongs to numerous s­ cientific and know it, you have no certainty until you try. educational organizations including the ­American Chemi- —Sophocles cal Society (ACS) and the National Science Teachers As- Discovery consists of seeing what everybody has seen and sociation (NSTA). She has been the ­Western Regional thinking what nobody has thought. Winner of the E ­ xcellence in C ­ ollege Chemistry Teaching —Albert Szent-Gyorgyi Award given by the Chemical Manufacturers Association. I never teach my pupils; I only attempt to provide the She received the McGuffey Award in Physical Sciences conditions in which they can learn. from the Textbook Authors Association for her textbook —Albert Einstein 15 Preface Welcome to the thirteenth edition of An Introduction to ­General, NEW! TEST feature added in the margin encourages Organic, and Biological Chemistry. This chemistry text was students to solve related Practice Problems to practice written and designed to help you prepare for a career in a retrieval of content for exams. health-related profession, such as nursing, dietetics, respiratory NEW! Interactive Videos give students the experi- therapy, and environmental and agricultural science. This text ence of step-by-step problem solving for problems from assumes no prior knowledge of chemistry. My main objective in the text. writing this text is to make the study of chemistry an ­engaging NEW! Review topics placed in the margin at the begin- and positive experience for you by relating the structure and ning of a section list the Key Math Skills and Core behavior of matter to its role in health and the environment. This ­Chemistry Skills from the previous chapters, which pro- new edition introduces more problem-solving strategies, more vide the foundation for learning new chemistry princi- problem-solving guides, new Analyze the Problem with Con- ples in the current chapter. nect features, new Try It First and Engage features, conceptual UPDATED! Solution Guides are now included in and challenge problems, and new sets of combined problems. selected Sample Problems. It is my goal to help you become a critical thinker by UPDATED! Key Math Skills review basic math relevant understanding scientific concepts that will form a basis for to the chemistry the students are learning throughout making important decisions about issues concerning health and the text. A Key Math Skill Review at the end of each the environment. Thus, I have utilized materials that ­chapter summarizes and gives additional examples. UPDATED! Core Chemistry Skills identify the key help you to learn and enjoy chemistry chemical principles in each chapter that are required relate chemistry to careers that interest you for successfully learning chemistry. A Core Chemistry develop problem-solving skills that lead to your success Skill Review at the end of each chapter helps reinforce in chemistry the material and gives additional examples. promote learning and success in chemistry UPDATED! Analyze the Problem features included in the solutions of the Sample Problems strengthen New for the Thirteenth Edition critical-thinking skills and illustrate the breakdown of a New and updated features have been added throughout this word problem into the components required to solve it. ­thirteenth edition, including the following: UPDATED! Practice Problems, Sample Problems, and art demonstrate the connection between the chemistry NEW AND UPDATED! Chapter Openers provide engag- being discussed and how these skills will be needed in ing clinical stories in the health profession and introduce the professional experience. chemical concepts in each chapter. UPDATED! Combining Ideas features offer sets of inte- NEW! Clinical Updates added at the end of each ­chapter grated problems that test students’ understanding and continue the story of the chapter opener and describe the develop critical thinking by integrating topics from two follow-up treatment. or more previous chapters. NEW! Engage feature in the margin asks students to think about the paragraph they are reading and to test their understanding by answering the Engage question, Chapter Organization of the which is related to the topic. NEW! Try It First precedes the solution section of each Thirteenth Edition Sample Problem to encourage the student to work on the In each textbook I write, I consider it essential to relate every problem before reading the given solution. chemical concept to real-life issues. Because a chemistry course NEW! Connect feature added to Analyze the Problem may be taught in different time frames, it may be difficult to boxes indicates the relationships between Given and cover all the chapters in this text. However, each chapter is a Need. complete package, which allows some chapters to be skipped or NEW! Clinical Applications added to Practice Problems the order of presentation to be changed. show the relevance between the chemistry content and medicine and health. Chapter 1, Chemistry in Our Lives, discusses the Scien- NEW! Strategies for Learning Chemistry are added tific Method in everyday terms, guides students in developing that utilize successful ways to study and learn chemistry. a study plan for learning chemistry, with a section of Key Math 16  Preface 17 Skills that reviews the basic math, including scientific notation, Chapter 3, Matter and Energy, classifies matter and states needed in chemistry calculations. of matter, describes temperature measurement, and discusses energy, specific heat, energy in nutrition, and changes of state. The Chapter Opener tells the story of a murder and fea- Physical and chemical properties and physical and chemical tures the work and career of forensic scientists. changes are discussed. A new Clinical Update feature describes the forensic ­evidence that helps to solve the murder and includes The chapter opener describes diet and exercise for an Clinical Applications. overweight adolescent at risk for type 2 diabetes and fea- “Scientific Method: Thinking Like a Scientist” is tures the work and career of a dietitian. expanded to include law and theory. A new Clinical Update describes the new diet prepared Writing Numbers in Scientific Notation is now a new with a dietitian for weight loss. Section. Practice Problems and Sample Problems include high An updated Section titled Studying and Learning Chem- temperatures used in cancer treatment, the energy pro- istry expands the discussion of strategies that improve duced by a high-energy shock output of a defibrillator, learning and understanding of content. body temperature lowering using a cooling cap, ice bag Key Math Skills are: Identifying Place Values, Using therapy for muscle injury, and energy values for food. Positive and Negative Numbers in Calculations, Cal- Core Chemistry Skills are: Identifying Physical and culating Percentages, Solving Equations, Interpreting Chemical Changes, Converting between Temperature Graphs, and Writing Numbers in Scientific Notation. Scales, Using Energy Units, Using the Heat Equation, and Calculating Heat for Change of State. Chapter 2, Chemistry and Measurements, looks at meas- The interchapter problem set, Combining Ideas from urement and emphasizes the need to understand ­numerical Chapters 1 to 3, completes the chapter. relationships of the metric system. Significant figures are dis- Chapter 4, Atoms and Elements, introduces elements and cussed in the determination of final answers. Prefixes from the atoms and the periodic table. The names and symbols for the metric system are used to write equalities and conversion fac- newest elements 113, Nihonium, Nh, 115, Moscovium, Mc, tors for problem-solving strategies. Density is discussed and 117, Tennessine, Ts, and 118, Oganesson, Og, are added to the used as a conversion factor. periodic table. Electron arrangements are written for atoms and The Chapter Opener tells the story of a patient with high the trends in periodic properties are described. Atomic numbers blood pressure and features the work and career of a reg- and mass numbers are determined for isotopes. The most abun- istered nurse. dant isotope of an element is determined by its atomic mass. A new Clinical Update describes the patient’s status and The Chapter Opener and Follow Up feature the work and follow-up visit with his doctor. career of a farmer. New photos, including an endoscope, propranolol tab- A new Clinical Update describes the improvement in lets, cough syrup, people exercising, a urine dipstick, and crop production by the farmer. a pint of blood, are added to improve visual introduc- Atomic number and mass number are used to calculate tion to clinical applications of chemistry. Previous art is the number of protons and neutrons in an atom. updated to improve clarity. The number of protons and neutrons are used to calculate Sample Problems relate problem solving to health- the mass number and to write the atomic symbol for an related topics such as the measurements of blood isotope. ­volume, omega-3 fatty acids, radiological imaging, body The trends in periodic properties are described for fat, ­cholesterol, and medication orders. valence electrons, atomic size, ionization energy, and New Clinical Applications feature questions about meas- metallic character. urements, daily values for minerals and vitamins, equali- Core Chemistry Skills are: Counting Protons and ties and conversion factors for medications. ­Neutrons, Writing Atomic Symbols for Isotopes, Writing New material illustrates how to count significant figures Electron Arrangements, Identifying Trends in Periodic in equalities and in conversion factors used in a problem Properties, and Drawing Lewis Symbols. setup. A new Key Math Skill, Rounding Off, has been added. Chapter 5, Nuclear Chemistry, looks at the types of radia- Core Chemistry Skills are: Counting Significant Figures, tion emitted from the nuclei of radioactive atoms. Nuclear Using Significant Figures in Calculations, Using Pre- equations are written and balanced for both naturally occurring fixes, Writing Conversion Factors from Equalities, Using radioactivity and artificially produced radioactivity. The half- Conversion Factors, and Using Density as a Conversion lives of radioisotopes are discussed, and the amount of time for Factor. a sample to decay is calculated. Radioisotopes important in the 18 Preface field of nuclear medicine are described. Fission and fusion and of particles in a given quantity of an element or a substance. their role in energy production are discussed. Students learn to balance chemical equations and to recognize the types of chemical reactions: combination, decomposition, The new chapter opener describes a patient with pos- single replacement, double replacement, and combustion. sible coronary heart disease who undergoes a nuclear Chapter discussion includes Oxidation–­Reduction Reactions stress test and features the work and career of a radiation using real-life examples, including biological reactions, Mole technologist. Relationships in Chemical Equations, Mass Calculations for A new Clinical Update discusses the results of cardiac Chemical Reactions, and Energy in Chemical Reactions, which imaging using the radioisotope Tl-201. discusses activation energy and energy changes in exothermic Sample Problems and Practice Problems use nursing and and endothermic reactions. medical examples, including p­ hosphorus-32 for the treat- ment of leukemia, titanium seeds containing a radioac- The chapter opener describes the symptoms of pulmo- tive isotope implanted in the body to treat cancer, yttrium nary emphysema and discusses the career of an exercise injections for arthritis pain, and millicuries in a dose of physiologist. phosphorus-32. A new Clinical Update explains the treatment for intersti- Core Chemistry Skills are: Writing Nuclear Equations tial lung disease. and Using Half-Lives. Sample Problems and Challenge Problems use nursing and medical examples. Chapter 6, Ionic and Molecular Compounds, describes New expanded art shows visible evidence of a chemical the formation of ionic and covalent bonds. Chemical formulas reaction. are written, and ionic compounds—including those with poly­ Core Chemistry Skills are: Converting Particles to Moles, atomic ions—and molecular compounds are named. Calculating Molar Mass, Using Molar Mass as a Conver- The chapter opener describes aspirin as a molecular com- sion Factor, Balancing a Chemical Equation, Classifying pound and features the work and career of a pharmacy Types of Chemical Reactions, Identifying Oxidized and technician. Reduced Substances, Using Mole–Mole Factors, and A new Clinical Update describes several types of com- Converting Grams to Grams. pounds at a pharmacy and includes Clinical Applications. Section 6.6 is now titled “Lewis Structures for Mole- Chapter 8, Gases, discusses the properties of gases and cal- cules,” 6.7 is “Electronegativity and Bond Polarity,” 6.8 culates changes in gases using the gas laws: Boyle’s, Charles’s, is “Shapes of Molecules,” and 6.9 is “Polarity of Mol- Gay-Lussac’s, Avogadro’s, and Dalton’s. Problem-solving strat- ecules and Intermolecular Forces.” egies enhance the discussion and calculations with gas laws. The term Lewis structure has replaced the term electron- The chapter opener features the work and career of a res- dot formula. piratory therapist. Updated material on polyatomic ions compares the New Clinical Update describes exercise to prevent names of ate ions and ite ions, the charge of carbonate ­e xercise-induced asthma. Clinical Applications are and hydrogen carbonate, and the formulas and charges of related to lung volume and gas laws. halogen polyatomic ions with oxygen. Sample Problems and Challenge Problems use nursing A new art comparing the particles and bonding of ionic and medical examples, including, calculating the ­volume compounds and molecular compounds has been added. of oxygen gas delivered through a face mask during A new flowchart for naming chemical compounds in ­oxygen therapy, preparing a heliox breathing mixture for Section 6.5 shows naming patterns for ionic and molecu- a scuba diver, and home oxygen tanks. lar compounds. Core Chemistry Skills are: Using the Gas Laws and Core Chemistry Skills are: Writing Positive and ­Negative ­Calculating Partial Pressure. Ions, Writing Ionic Formulas, Naming Ionic ­Compounds, Writing the Names and Formulas for Molecular Com- Chapter 9, Solutions, describes solutions, electrolytes, satura- pounds, Drawing Lewis Structures, Using Electron- tion and solubility, insoluble salts, concentrations, and osmosis. egativity, Predicting Shape, and Identifying Polarity of The concentrations of solutions are used to determine volume or Molecules and Intermolecular Forces. mass of solute. The volumes and molarities of solutions are used The interchapter problem set, Combining Ideas from in calculations of dilutions and titrations. Properties of solutions, Chapters 4 to 6, completes the chapter. osmosis in the body, and dialysis are discussed. Chapter 7, Chemical Quantities and Reactions, ­discusses The chapter opener describes a patient with kidney fail- Avogadro’s number, the mole, and molar masses of compounds, ure and dialysis treatment and features the work and which are used in calculations to determine the mass or number career of a dialysis nurse.  Preface 19 A new Clinical Update explains dialysis treatment and Core Chemistry Skills are: Naming and Drawing electrolyte levels in dialysate fluid. Alkanes and Writing Equations for Hydrogenation and Art updates include gout and intravenous solutions. Hydration. Table 9.6 on electrolytes in intravenous solutions is expanded. Chapter 12, Alcohols, Thiols, Ethers, Aldehydes, and Core Chemistry Skills are: Using Solubility Rules, Cal- Ketones, describes the functional groups and names of alco- culating Concentration, and Using Concentration as a hols, thiols, ethers, aldehydes, and ketones. The solubility of Conversion Factor. alcohols, phenols, aldehydes, and ketones in water is discussed. The interchapter problem set, Combining Ideas from A new chapter opener describes the risk factors for mela- Chapters 7 to 9, completes the chapter. noma and discusses work and career of a dermatology nurse. Chapter 10, Acids and Bases and Equilibrium, discusses A new Clinical Update discusses melanoma, skin protec- acids and bases and conjugate acid–base pairs. The dissociation tion, and functional groups of sunscreens. of strong and weak acids and bases is related to their strengths A table Solubility of Selected Aldehydes and Ketones as acids or bases. The dissociation of water leads to the water has been updated. dissociation expression, Kw, the pH scale, and the calculation New material on antiseptics is added. of pH. The reactions of acids and bases with metals, carbon- The oxidation of methanol in the body is included in the ates, and bicarbonates are discussed. Chemical equations for Chemistry Link to Health “Oxidation of Alcohol in the acids in reactions are balanced and titration of an acid is illus- Body.” trated. Buffers are discussed along with their role in the blood. Core Chemistry Skills are: Identifying Functional Groups, Naming Alcohols and Phenols, Naming Alde- The chapter opener describes an accident victim with hydes and Ketones, Writing Equations for the Dehydra- respiratory acidosis and the work and career of a clinical tion of Alcohols, and Writing Equations for the Oxidation laboratory technician. of Alcohols. A Clinical Update discusses the symptoms and treatment The interchapter problem set, Combining Ideas from for acid reflux disease. Chapters 10 to 12, completes the chapter. The section “Acid–Base Equilibrium” includes Le Châtelier’s principle. Chapter 13, Carbohydrates, describes the carbohydrate Clinical Applications include calculating [OH - ] or molecules monosaccharides, disaccharides, and polysaccha- [H3 O + ] of body fluids, foods, blood plasma, and the pH rides and their formation by photosynthesis. Monosaccharides of body fluids. are classified as aldo or keto pentoses or hexoses. Chiral mol- Key Math Skills are: Calculating pH from [H3O+ ] and ecules are discussed along with Fischer projections and d and Calculating [H3O+ ] from pH. l notations. Chiral objects are modeled using gumdrops and New Core Chemistry Skills are: Identifying Conjugate toothpicks. Carbohydrates used as sweeteners are described Acid–Base Pairs, Using Le Chatelier’s Principle, Cal- and carbohydrates used in blood typing are discussed. The for- culating [H3O+ ] and [OH - ] in Solutions, Writing Equa- mation of glycosidic bonds in disaccharides and polysaccha- tions for Reactions of Acids and Bases, and Calculating rides is described. Molarity or Volume of an Acid or Base in a Titration. A chapter opener describes a diabetes patient and her diet and features the work and career of a diabetes nurse. Chapter 11, Introduction to Organic Chemistry: Hydro- A new Clinical Update describes a diet to lower blood carbons, compares inorganic and organic compounds, and glucose. describes the structures and naming of alkanes, alkenes includ- Chiral molecules are discussed and Fischer projections ing cis–trans isomers, alkynes, and aromatic compounds. are drawn. The chapter opener describes a fire victim and the search A new Sample Problem identifies chiral carbons in glyc- for traces of accelerants and fuel at the arson scene and erol and ibuprofen. features the work and career of a firefighter/emergency New art shows that insulin needed for the metabolism of medical technician. glucose is produced in the pancreas. A new Clinical Update describes the treatment of burns Examples of chiral molecules in nature are included to in the hospital and the types of fuels identified in the fire. Chemistry Link to Health, “Enantiomers in Biological Wedge–dash models have been added to the representa- Systems.” tions of methane and ethane. New Clinical Applications include psicose in foods, Line-angle formulas are now included in Table 11.2 ­lyxose in bacterial glycolipids, xylose in absorption tests, IUPAC Names and Formulas of the First Ten Alkanes. and tagatose in fruit. 20 Preface New art shows the rotation of groups on carbon 5 for the Chapter 16, Amino Acids, Proteins, and Enzymes, dis- Haworth structures of glucose and galactose. cusses amino acids, formation of peptide bonds and proteins, Drawing Haworth Structures is updated. structural levels of proteins, enzymes, and enzyme action. The Chemistry Link to Health “Blood Types and Carbo- The structures of amino acids are drawn at physiological pH. hydrates” has updated structures of the saccharides that Enzymes are discussed as biological catalysts, along with the determine each blood type. impact of inhibitors and denaturation on enzyme action. Core Chemistry Skills are: Identifying Chiral Molecules, A new chapter opener discusses the symptoms of sickle- Identifying d and l Fischer Projections, and Drawing cell anemia in a child, the mutation in amino acids that Haworth Structures. causes the crescent shape of abnormal red blood cells, Chapter 14, Carboxylic Acids, Esters, Amines, and and the career of a physician assistant. Amides, discusses the functional groups and naming of car- The use of electrophoresis to diagnose sickle-cell ­anemia boxylic acids, esters, amines, and amides. Chemical reactions was added to Chemistry Link to Health “Sickle-Cell include esterification, amidation, and acid and base hydrolysis Anemia.” of esters and amides. Abbreviations for amino acid names use three letters as well as one letter. A chapter opener describes pesticides and pharmaceuti- New ribbon models of beta-amyloid proteins in normal cals used on a ranch and discusses the career of an envi- brain and an Alzheimer’s brain are added to ­Chemistry ronmental health practitioner. Link to Health “Protein Secondary Structures and A new Clinical Update describes an insecticide used to ­Alzheimer’s Disease”. spray animals. Diagrams illustrate enzyme action and the effect of Line-angle structures for carboxylic acids are added to competitive and noncompetitive inhibitors on enzyme Table 14.1. structure. Core Chemistry Skills are: Naming Carboxylic Acids, Core Chemistry Skills are: Drawing the Structure for an Hydrolyzing Esters, and Forming Amides. Amino Acid at Physiological pH, Identifying the Pri- mary, Secondary, Tertiary, and Quaternary Structures of Chapter 15, Lipids, discusses fatty acids and the formation Proteins, and Describing Enzyme Action. of ester bonds in triacylglycerols and glycerophospholipids. Chemical properties of fatty acids and their melting points Chapter 17, Nucleic Acids and Protein Synthesis, along with the hydrogenation of unsaturated triacylglycerols describes the nucleic acids and their importance as biomole- are discussed. Steroids, such as cholesterol and bile salts, are cules that store and direct information for the synthesis of cel- described. Chemistry Links to Health include “Converting lular components. The role of complementary base pairing is Unsaturated Fats to Saturated Fats: Hydrogenation.” The role discussed in both DNA replication and the formation of mRNA of phospholipids in the lipid bilayer of cell membranes is dis- during protein synthesis. The role of RNA is discussed in the cussed as well as the lipids that function as steroid hormones. relationship of the genetic code to the sequence of amino acids A new chapter opener describes a patient with symptoms in a protein. Mutations describe ways in which the nucleotide of familial hypercholesterolemia and features the work sequences are altered in genetic diseases. and career of a clinical lipid specialist. A new chapter opener describes a patient’s diagnosis and A new Clinical Update describes a program to lower treatment of breast cancer and discusses the work and cholesterol. career of a histology technician. New notation for number of carbon atoms and double A new Clinical Update describes estrogen-positive bonds in a fatty acid is added. tumors, the impact of the altered genes BRCA1 and New art of unsaturated fatty acids with cis and trans dou- BRCA2 on the estrogen receptor, and medications to ble bonds is added. suppress tumor growth. New art of normal and damaged myelin sheath shows A new Section discusses recombinant DNA, polymerase deterioration in multiple sclerosis. chain reaction, and DNA fingerprinting. New art of the gallbladder and the bile duct where gall- New art illustrates point mutation, deletion mutation, and stones pass causing obstruction and pain. insertion mutation. Core Chemistry Skills are: Identifying Fatty Acids, Core Chemistry Skills are: Writing the Complementary DNA Drawing Structures for Triacylglycerols, Drawing the Strand, Writing the mRNA Segment for a DNA ­Template, Products for the Hydrogenation, Hydrolysis, and Saponi- and Writing the Amino Acid for an mRNA Codon. fication of a Triacylglycerol, and Identifying the Steroid Nucleus. Chapter 18, Metabolic Pathways and ATP P ­ roduction, The interchapter problem set, Combining Ideas from describes the metabolic pathways of biomolecules from the Chapters 13 to 15, completes the chapter. digestion of foodstuffs to the synthesis of ATP. The stages of  Preface 21 catabolism and the digestion of carbohydrates along with the Updated art for glycolysis, the citric acid cycle, and elec- coenzymes required in metabolic pathways are described. The tron transport is added. breakdown of glucose to pyruvate is described using glycoly- The values of ATP produced from the metabolism of glu- sis, which is followed by the decarboxylation of pyruvate to cose, fatty acids, and amino acids is calculated using the acetyl CoA and the entry of acetyl CoA into the citric acid updated values of 2.5 ATP for NADH and 1.5 ATP for cycle. Electron transport, oxidative phosphorylation, and the FADH2. synthesis of ATP is described. The oxidation of lipids and the Core Chemistry Skills are: Identifying the Compounds degradation of amino acids are also discussed. in Glycolysis, Describing the Reactions in the Citric Acid Cycle, Calculating the ATP Produced from Glu- A new chapter opener describes elevated levels of liver cose, and Calculating the ATP from Fatty Acid Oxidation enzymes for a patient with chromic hepatitis C infection (b ­Oxidation). and discusses the career of a public health nurse. The interchapter problem set, Combining Ideas from A new Clinical Update describes interferon and ribavirin Chapters 16 to 18, completes the chapter. therapy for hepatitis C. Acknowledgments The preparation of a new text is a continuous effort of many thank Wynne Au Yeung and Stephanie Marquez, art specialists; people. I am thankful for the support, encouragement, and Mark Ong and Tamara Newnam, interior and cover designers, dedication of many people who put in hours of tireless effort to whose creative ideas provided the outstanding design for the produce a high-quality book that provides an outstanding learn- cover and pages of the book. Eric Shrader, photo researcher, was ing package. I am thankful for the outstanding contributions of outstanding in researching and selecting vivid photos for the text Professor MaryKay Orgill whose updates and clarifications en- so that students can see the beauty of chemistry. Thanks also to hanced the content of the biochemistry chapters 16 to 18. The Bio-Rad Laboratories for their courtesy and use of KnowItAll editorial team at Pearson has done an exceptional job. I want to ChemWindows, drawing software that helped us produce chemi- thank Jeanne Zalesky, Director, Courseware Portfolio Manage- cal structures for the manuscript. The macro-to-micro illustra- ment, and Scott Dustan, Courseware Portfolio Manager, who tions designed by Production Solutions and Precision Graphics supported our vision of this thirteenth edition. give students visual impressions of the atomic and molecular I appreciate all the wonderful work of Lizette Faraji, organization of everyday things and are a fantastic learning tool. ­Content Producer, who skillfully brought together reviews, I also appreciate all the hard work in the field put in by the mar- art, web site materials, and all the things it takes to prepare a keting team and Elizabeth Ellsworth, marketing manager. book for production. I appreciate the work of Karen Berry and I am extremely grateful to an incredible group of peers for ­Christian Arsenault at SPi Global, who brilliantly coordinated all their careful assessment of all the new ideas for the text; for phases of the manuscript to the final pages of a beautiful book. their suggested additions, corrections, changes, and deletions; Thanks to Mark Quirie, manuscript and accuracy reviewer, and and for providing an incredible amount of feedback about Laura Patchkofsky and Linda Smith, who precisely analyzed improvements for the book. I admire and appreciate every one and edited the initial and final manuscripts and pages to make of you. sure the words and problems were correct to help students learn If you would like to share your experience with chemistry, chemistry. Their keen eyes and thoughtful comments were or have questions and comments about this text, I would appre- extremely helpful in the development of this text. ciate hearing from you. I am especially proud of the art program in this text, which Karen Timberlake lends beauty and understanding to chemistry. I would like to Email: [email protected] Acknowledgments for the Global Edition Pearson would like to acknowledge and thank Chitralekha Trzcinski, the University of Southern Queensland, for reviewing Sidana for contributing to the Global Edition, and Karishma the Global Edition. Kochar, Dr. S. Nehru, University of Madras, and Antoine A01_TIMB8860_13_GE_FM.indd 21 16/03/2018 10:47  Instructor and Student Supplements Chemistry: An Introduction to General, Organic, and Biological Chemistry, thirteenth edition, provides an integrated teaching and learning package of support material for both students and professors. Instructor Available Available or Student Name of Supplement in Print Online Supplement Description ™ Mastering Chemistry ✓ Supplement This product includes all of the resources of Mastering™ Chemistry. Mastering™ (www.masteringchemistry for Students Chemistry from Pearson is the leading online homework, tutorial, and assessment.com) and Instructors system, designed to improve results by engaging students with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content and encourage critical thinking and retention with in-class resources such as Learning Catalytics™. Students can further master concepts through ­traditional and adaptive homework assignments that provide hints and answer specific feedback. The Mastering™ gradebook records scores for all assignments in one place, while diagnostic tools give instructors access to rich data to assess student understanding and misconceptions. http://www.masteringchemistry.com. Pearson eText ✓ Supplement The thirteenth edition of Chemistry: An Introduction to General, Organic, and for Students Biological Chemistry features a Pearson eText within Mastering. In conjunction with Mastering assessment capabilities, new Interactive Videos and 3D animations will improve student engagement and knowledge retention. Each chapter contains a balance of interactive animations, videos, sample calculations, and self-assessments / quizzes. Icons in the margins throughout the text signify that there is a new Interactive Video or animation located within Mastering™ Chemistry for Chemistry: An Introduction to General, Organic, and Biological Chemistry, thirteenth edition. Laboratory Manual by ✓ Supplement This best-selling lab manual coordinates 35 experiments with the topics in Karen Timberlake for Students Chemistry: An Introduction to General, Organic, and Biological Chemistry, (9780321811851) thirteenth edition, uses laboratory investigations to explore chemical concepts, develop skills of manipulating equipment, reporting data, solving problems, making calculations, and drawing conclusions. Instructor’s Solutions ✓ Supplement Prepared by Mark Quirie, the Instructor’s Solutions Manual highlights chapter Manual for Instructors topics, and includes answers and solutions for all Practice Problems in the text. Instructor Resource ✓ Supplement Includes all the art, photos, and tables from the book in JPEG format for use in Materials–Download for Instructors classroom projection or when creating study materials and tests. In addition, the Only instructors can access modifiable PowerPoint™ lecture outlines. Also visit the Pearson Education catalog page for Timberlake’s Chemistry: An Introduction to General, Organic, Biological Chemistry, thirteenth edition, at www.pearsonglobaleditions.com/timberlake to download available instructor supplements. TestGen Test Bank- ✓ Supplement Prepared by William Timberlake, this resource includes more than 1600 questions Download Only for Instructors in multiple-choice, matching, true/false, and short-answer format. Online Instructor Manual ✓ Supplement This manual contains answers to report sheet pages for the Laboratory Manual for Laboratory Manual for Instructors and a list of the materials needed for each experiment with amounts given for 20 students working in pairs, available for download at www.pearsonglobaleditions.com/timberlake. 22 A01_TIMB8860_13_GE_FM.indd 22 16/03/2018 10:47  Career Focus Engages Students Best-selling author Karen Timberlake connects chemistry to real-world and career applications like no one else. The 13th edition of Chemistry: An Introduction to General, Organic, and Biological Chemistry engages students by helping them to see the connections between chemistry, the world around them, and future careers. Chapter Openers emphasize clinical connections by showing students relevant, engaging, topical examples of how health professionals use chemistry everyday. Clinical Updates at the end of each chapter relate the chemistry the student learns in the chapter to expand the clinical content in the Chapter Opener and include clinical applications. Chemistry Links to Health, ­ oven throughout each w ­chapter, apply chemical concepts to topics in health and medicine such as weight loss and weight gain, alcohol abuse, blood buffers, and kidney dialysis, illustrating the importance of understanding chemistry in real-life situations. A02_TIMB8860_13_GE_WALK.indd 23 07/03/18 5:00 PM  Builds Students’ Critical-Thinking and Problem-Solving Skills One of Karen Timberlake’s goals is to help students to become critical thinkers. Color- coded tips found throughout each chapter are designed to provide guidance and to encourage students to really think about what they are reading, helping to develop important critical-thinking skills. NEW! Review Feature lists the core chemistry skills and key math skills from ­previous ­chapters which ­provide the foundation for learning the new ­chemistry principles in the current chapter. NEW! Engage Feature asks students to think about the paragraph they are reading and immediately test their understanding by answering the Engage ­question, which is related to the topic. Students connect new concepts to prior knowledge to increase retrieval of content. UPDATED! Core ­Chemistry Skills found throughout the chapter identify the fundamen- tal chemistry concepts that students need to understand in the cur- rent chapt